Below are two formats for communicating with investors. Note that once you get to a certain stage/size, you may discontinue or limit broad investor outreach. At some point investors can start to become a source of leaks about the company.

LONG FORMAT INVESTOR UPDATES (FOR SERIES A OR REVENUE/USER GROWTH GENERATING COS)
This slightly longer email format (1-2 pages in an email) for companies with a launched product and some ongoing growth. Investor "Asks" should always come first (as some investors won't read much past the first section in the email). This way if you need help, investors will know how to help. This format usually works best for a company that is farther along (e.g. Series A company, or one producing revenue).

At some point you may decide to discontinue this format as the likelihood of leaks by investors goes up the later stage the company. You can also skip any of the items below if there are no updates.

1. Asks.
What do you need help with? List up to 3 items people can help you with. This should always go at the top of the email, as people might not read the rest in detail. If no relevant asks, skip this section.

2. 1-2 Key Metrics.
Month by month or other revenue metrics for the last 6-12 months. Include a graph and growth rates. Mention margin or other key financial metrics where relevant. User growth, retention, or other key metrics.

3. Team.
Who got hired last month? Write a sentence per person emphasizing the quality of the new hire. If you are growing rapidly (e.g. 5-10 people a month) you can instead focus on mentioning 1-2 key hires, team size, and team growth rate. E.g. "We are now 42 people (added 5 this month) including our new head of finance, ...."

5. Partnerships.
1-2 lines on one or two most important deals, if any.

6. Industry news.
1-2 news items, if very relevant or provides background to your company. If nothing big, don't mention anything. Could also be links to articles about your company.

7. Burn/cash.
Current cash position and burn rate. How many months or runway do you have left?

8. Other
Could include team photo from a fun event (e.g. Halloween) or other misc items (if any).

SHORT FORMAT MONTHLY UPDATE (SEED OR EARLY COMPANIES)
You can use this format either for earlier stage startups, or for broad lists of investors if later stage. This allows you to avoid too much detail while still getting help (investor asks).

1. Asks.
What do you need help with? List up to 3 items people can help you with. This should always go at the top of the email, as people might not read the rest in detail.

2. Highlights.
What went well this month? Could be a bulleted list of 2-5 items.

3. Lowlights.
What went poorly this month? Could be a bulleted list of 2-5 items.

OPERATIONALIZING IT

In order to maintain discipline on monthly emails, schedule some time on your calendar on e.g. the last Friday of the month to write the email and send it. Once you have sent an update once, you can use past emails as a template and it should be quite fast.